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. 2021 Nov 19;86(22):15847-15865.
doi: 10.1021/acs.joc.1c01609. Epub 2021 Oct 7.

Capitalizing on Mediated Electrolyses for the Construction of Complex, Addressable Molecular Surfaces

Ruby Krueger  1 , Kevin D Moeller  1
Affiliations

Capitalizing on Mediated Electrolyses for the Construction of Complex, Addressable Molecular Surfaces

Ruby Krueger et al. J Org Chem. .

Abstract

Synthetic organic chemists are beginning to exploit electrochemical methods in increasingly creative ways. This is leading to a surge in productivity that is only now starting to take advantage of the full-potential of electrochemistry for accessing new structures in novel, more efficient ways. In this perspective, we provide insight into the potential of electrochemistry as a synthetic tool gained through studies of both direct anodic oxidation reactions and more recent indirect methods, and highlight how the development of new electrochemical methods can expand the nature of synthetic problems our community can tackle.

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Figures

Scheme 1.
Scheme 1.
Electrochemistry and Umpolung Reactions (EWG = electron-withdrawing group, EDG = electron-donating group, Nu = nucleophile, E = electrophile).
Scheme 2.
Scheme 2.
A mediated or indirect electrolysis.
Scheme 3.
Scheme 3.
An initial problem – replacing spatially close protons with bridges.
Scheme 4.
Scheme 4.
Examples of the Shono oxidation.
Scheme 5.
Scheme 5.
Anodic Olefin Coupling Reactions.
Scheme 6.
Scheme 6.
Microelectrode arrays and biological studies.
Scheme 7.
Scheme 7.
The Lin Group and the oxidative functionalization of alkenes.
Scheme 8.
Scheme 8.
The Stahl Group and the use of co-mediators.
Scheme 9.
Scheme 9.
The Xu Group and the use of photoelectrocatalytic mediators.
Scheme 10.
Scheme 10.
The Baran Group and allylic oxidations.
Scheme 11.
Scheme 11.
The Little-group and the development of oxidative mediators.
Scheme 12.
Scheme 12.
The Wacker oxidation and a starting point.
Scheme 13.
Scheme 13.
A site-selective TEMPO oxidation.
Scheme 14.
Scheme 14.
An array based CAN oxidation.
Scheme 15.
Scheme 15.
A Pd(0)-catalyzed reaction conducted on an array.
Scheme 16.
Scheme 16.
The use of a Cu-(I)-catalyst.
Scheme 17.
Scheme 17.
A site-selective Diels-Alder reaction.
Scheme 18.
Scheme 18.
Characterization using a Kenner-type safety-catch linker.
Scheme 19.
Scheme 19.
Diblock copolymer surfaces for the arrays.
Scheme 20.
Scheme 20.
Tunable surfaces and the use of both reversible and irreversible transformations.
Scheme 21.
Scheme 21.
The synthesis of arylborates on a microelectrode array.
Scheme 22.
Scheme 22.
A new, orthoganol safety-catch linker strategy.
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References

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